diff --git a/CROSS_COMPILE.md b/CROSS_COMPILE.md
index 4728768..366fd23 100644
--- a/CROSS_COMPILE.md
+++ b/CROSS_COMPILE.md
@@ -5,6 +5,6 @@ $ sudo usermod -aG docker $USER
 $ exec sudo su -l $USER
 $ sudo systemctl start docker
 $ cargo install cross
-$ cross build --release --features tls_vendored --target armv7-unknown-linux-musleabihf
+$ cross build --release --target armv7-unknown-linux-musleabihf
 ```
 The cross-compiled binary is at target/armv7-unknown-linux-musleabihf/release/conduit
diff --git a/Cargo.lock b/Cargo.lock
index c5c79b8..84001dc 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -198,6 +198,8 @@ dependencies = [
  "rocket",
  "ruma",
  "rust-argon2",
+ "rustls",
+ "rustls-native-certs",
  "serde",
  "serde_json",
  "serde_yaml",
@@ -209,6 +211,7 @@ dependencies = [
  "tracing-opentelemetry",
  "tracing-subscriber",
  "trust-dns-resolver",
+ "webpki",
 ]
 
 [[package]]
@@ -420,21 +423,6 @@ version = "1.0.7"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "3f9eec918d3f24069decb9af1554cad7c880e2da24a9afd88aca000531ab82c1"
 
-[[package]]
-name = "foreign-types"
-version = "0.3.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f6f339eb8adc052cd2ca78910fda869aefa38d22d5cb648e6485e4d3fc06f3b1"
-dependencies = [
- "foreign-types-shared",
-]
-
-[[package]]
-name = "foreign-types-shared"
-version = "0.1.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "00b0228411908ca8685dba7fc2cdd70ec9990a6e753e89b6ac91a84c40fbaf4b"
-
 [[package]]
 name = "form_urlencoded"
 version = "1.0.1"
@@ -716,16 +704,18 @@ dependencies = [
 ]
 
 [[package]]
-name = "hyper-tls"
-version = "0.5.0"
+name = "hyper-rustls"
+version = "0.22.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d6183ddfa99b85da61a140bea0efc93fdf56ceaa041b37d553518030827f9905"
+checksum = "5f9f7a97316d44c0af9b0301e65010573a853a9fc97046d7331d7f6bc0fd5a64"
 dependencies = [
- "bytes",
+ "futures-util",
  "hyper",
- "native-tls",
+ "log",
+ "rustls",
  "tokio",
- "tokio-native-tls",
+ "tokio-rustls",
+ "webpki",
 ]
 
 [[package]]
@@ -1001,24 +991,6 @@ dependencies = [
  "winapi",
 ]
 
-[[package]]
-name = "native-tls"
-version = "0.2.7"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b8d96b2e1c8da3957d58100b09f102c6d9cfdfced01b7ec5a8974044bb09dbd4"
-dependencies = [
- "lazy_static",
- "libc",
- "log",
- "openssl",
- "openssl-probe",
- "openssl-sys",
- "schannel",
- "security-framework",
- "security-framework-sys",
- "tempfile",
-]
-
 [[package]]
 name = "ntapi"
 version = "0.3.6"
@@ -1096,49 +1068,12 @@ version = "1.7.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "af8b08b04175473088b46763e51ee54da5f9a164bc162f615b91bc179dbf15a3"
 
-[[package]]
-name = "openssl"
-version = "0.10.33"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a61075b62a23fef5a29815de7536d940aa35ce96d18ce0cc5076272db678a577"
-dependencies = [
- "bitflags",
- "cfg-if",
- "foreign-types",
- "libc",
- "once_cell",
- "openssl-sys",
-]
-
 [[package]]
 name = "openssl-probe"
 version = "0.1.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "77af24da69f9d9341038eba93a073b1fdaaa1b788221b00a69bce9e762cb32de"
 
-[[package]]
-name = "openssl-src"
-version = "111.15.0+1.1.1k"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b1a5f6ae2ac04393b217ea9f700cd04fa9bf3d93fae2872069f3d15d908af70a"
-dependencies = [
- "cc",
-]
-
-[[package]]
-name = "openssl-sys"
-version = "0.9.61"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "313752393519e876837e09e1fa183ddef0be7735868dced3196f4472d536277f"
-dependencies = [
- "autocfg",
- "cc",
- "libc",
- "openssl-src",
- "pkg-config",
- "vcpkg",
-]
-
 [[package]]
 name = "opentelemetry"
 version = "0.12.0"
@@ -1280,12 +1215,6 @@ version = "0.1.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "8b870d8c151b6f2fb93e84a13146138f05d02ed11c7e7c54f8826aaaf7c9f184"
 
-[[package]]
-name = "pkg-config"
-version = "0.3.19"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3831453b3449ceb48b6d9c7ad7c96d5ea673e9b470a1dc578c2ce6521230884c"
-
 [[package]]
 name = "png"
 version = "0.16.8"
@@ -1486,15 +1415,6 @@ version = "0.6.23"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "24d5f089152e60f62d28b835fbff2cd2e8dc0baf1ac13343bef92ab7eed84548"
 
-[[package]]
-name = "remove_dir_all"
-version = "0.5.3"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3acd125665422973a33ac9d3dd2df85edad0f4ae9b00dafb1a05e43a9f5ef8e7"
-dependencies = [
- "winapi",
-]
-
 [[package]]
 name = "reqwest"
 version = "0.11.3"
@@ -1509,19 +1429,20 @@ dependencies = [
  "http",
  "http-body",
  "hyper",
- "hyper-tls",
+ "hyper-rustls",
  "ipnet",
  "js-sys",
  "lazy_static",
  "log",
  "mime",
- "native-tls",
  "percent-encoding",
  "pin-project-lite",
+ "rustls",
+ "rustls-native-certs",
  "serde",
  "serde_urlencoded",
  "tokio",
- "tokio-native-tls",
+ "tokio-rustls",
  "url",
  "wasm-bindgen",
  "wasm-bindgen-futures",
@@ -1886,6 +1807,18 @@ dependencies = [
  "webpki",
 ]
 
+[[package]]
+name = "rustls-native-certs"
+version = "0.5.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5a07b7c1885bd8ed3831c289b7870b13ef46fe0e856d288c30d9cc17d75a2092"
+dependencies = [
+ "openssl-probe",
+ "rustls",
+ "schannel",
+ "security-framework",
+]
+
 [[package]]
 name = "ryu"
 version = "1.0.5"
@@ -2191,20 +2124,6 @@ dependencies = [
  "unicode-xid",
 ]
 
-[[package]]
-name = "tempfile"
-version = "3.2.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "dac1c663cfc93810f88aed9b8941d48cabf856a1b111c29a40439018d870eb22"
-dependencies = [
- "cfg-if",
- "libc",
- "rand",
- "redox_syscall 0.2.5",
- "remove_dir_all",
- "winapi",
-]
-
 [[package]]
 name = "termcolor"
 version = "1.1.2"
@@ -2358,16 +2277,6 @@ dependencies = [
  "syn",
 ]
 
-[[package]]
-name = "tokio-native-tls"
-version = "0.3.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f7d995660bd2b7f8c1568414c1126076c13fbb725c40112dc0120b78eb9b717b"
-dependencies = [
- "native-tls",
- "tokio",
-]
-
 [[package]]
 name = "tokio-rustls"
 version = "0.22.0"
@@ -2613,12 +2522,6 @@ dependencies = [
  "percent-encoding",
 ]
 
-[[package]]
-name = "vcpkg"
-version = "0.2.11"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b00bca6106a5e23f3eee943593759b7fcddb00554332e856d990c893966879fb"
-
 [[package]]
 name = "version_check"
 version = "0.9.3"
diff --git a/Cargo.toml b/Cargo.toml
index 57b6f7f..fa495df 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -49,7 +49,11 @@ rand = "0.8.3"
 # Used to hash passwords
 rust-argon2 = "0.8.3"
 # Used to send requests
-reqwest = { version = "0.11.1" }
+reqwest = { version = "0.11.3", default-features = false, features = ["rustls-tls-native-roots"] }
+# Custom TLS verifier
+rustls = { version = "0.19", features = ["dangerous_configuration"] }
+rustls-native-certs = "0.5.0"
+webpki = "0.21.0"
 # Used for conduit::Error type
 thiserror = "1.0.24"
 # Used to generate thumbnails for images
@@ -75,7 +79,6 @@ pretty_env_logger = "0.4.0"
 [features]
 default = ["conduit_bin"]
 conduit_bin = [] # TODO: add rocket to this when it is optional
-tls_vendored = ["reqwest/native-tls-vendored"]
 
 [[bin]]
 name = "conduit"
diff --git a/src/database/globals.rs b/src/database/globals.rs
index bad9c89..e48c849 100644
--- a/src/database/globals.rs
+++ b/src/database/globals.rs
@@ -10,13 +10,16 @@ use std::{
     time::Duration,
 };
 use trust_dns_resolver::TokioAsyncResolver;
+use rustls::{ServerCertVerifier, WebPKIVerifier};
 
 pub const COUNTER: &str = "c";
 
 type WellKnownMap = HashMap<Box<ServerName>, (String, String)>;
+type TlsNameMap = HashMap<String, webpki::DNSName>;
 #[derive(Clone)]
 pub struct Globals {
     pub actual_destination_cache: Arc<RwLock<WellKnownMap>>, // actual_destination, host
+    pub tls_name_override: Arc<RwLock<TlsNameMap>>,
     pub(super) globals: sled::Tree,
     config: Config,
     keypair: Arc<ruma::signatures::Ed25519KeyPair>,
@@ -26,6 +29,33 @@ pub struct Globals {
     pub(super) servertimeout_signingkey: sled::Tree, // ServerName + Timeout Timestamp -> algorithm:key + pubkey
 }
 
+struct MatrixServerVerifier {
+    inner: WebPKIVerifier,
+    tls_name_override: Arc<RwLock<TlsNameMap>>,
+}
+
+impl ServerCertVerifier for MatrixServerVerifier {
+    fn verify_server_cert(
+        &self,
+        roots: &rustls::RootCertStore,
+        presented_certs: &[rustls::Certificate],
+        dns_name: webpki::DNSNameRef<'_>,
+        ocsp_response: &[u8],
+    ) -> std::result::Result<rustls::ServerCertVerified, rustls::TLSError> {
+        let cache = self.tls_name_override.read().unwrap();
+        log::debug!("Searching for override for {:?}", dns_name);
+        log::debug!("Cache: {:?}", cache);
+        let override_name = match cache.get(dns_name.into()) {
+            Some(host) => {
+                log::debug!("Override found! {:?}", host);
+                host.as_ref()
+            },
+            None => dns_name
+        };
+        self.inner.verify_server_cert(roots, presented_certs, override_name, ocsp_response)
+    }
+}
+
 impl Globals {
     pub fn load(
         globals: sled::Tree,
@@ -66,10 +96,17 @@ impl Globals {
             }
         };
 
+        let tls_name_override = Arc::new(RwLock::new(TlsNameMap::new()));
+        let verifier = Arc::new(MatrixServerVerifier { inner: WebPKIVerifier::new(), tls_name_override: tls_name_override.clone() });
+        let mut tlsconfig = rustls::ClientConfig::new();
+        tlsconfig.dangerous().set_certificate_verifier(verifier);
+        tlsconfig.root_store = rustls_native_certs::load_native_certs().expect("Error loading system certificates");
+
         let reqwest_client = reqwest::Client::builder()
             .connect_timeout(Duration::from_secs(30))
             .timeout(Duration::from_secs(60 * 3))
             .pool_max_idle_per_host(1)
+            .use_preconfigured_tls(tlsconfig)
             .build()
             .unwrap();
 
@@ -86,7 +123,8 @@ impl Globals {
             dns_resolver: TokioAsyncResolver::tokio_from_system_conf().map_err(|_| {
                 Error::bad_config("Failed to set up trust dns resolver with system config.")
             })?,
-            actual_destination_cache: Arc::new(RwLock::new(HashMap::new())),
+            actual_destination_cache: Arc::new(RwLock::new(WellKnownMap::new())),
+            tls_name_override,
             servertimeout_signingkey,
             jwt_decoding_key,
         })
diff --git a/src/server_server.rs b/src/server_server.rs
index 5b49472..1bee9d5 100644
--- a/src/server_server.rs
+++ b/src/server_server.rs
@@ -74,6 +74,16 @@ where
             .write()
             .unwrap()
             .insert(Box::<ServerName>::from(destination), result.clone());
+        let actual_destination = result.0.strip_prefix("https://").unwrap().splitn(2, ':').next().unwrap();
+        let host = result.1.splitn(2, ':').next().unwrap_or(&result.1);
+        if actual_destination != host {
+            globals.tls_name_override.write().unwrap().insert(
+                actual_destination.to_owned(),
+                webpki::DNSNameRef::try_from_ascii_str(&host)
+                    .unwrap()
+                    .to_owned(),
+            );
+        }
         result
     };